Reaktion #5767

Reaktionsgleichung

water

2-(1-methylethyl)-5,9,13-trimethyl-2,4,8,12-cyclotetradecatetraen-1-one

diisobutyl aluminium hydride

hexane ethyl acetate

→

sarcophytol A

Ausbeute 90.3%

Lösungsmittel

toluene

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeOne hour
2. 2
   Trocknenby drying over MgSO4, filtration, and concentration
3. 3
   Sonstigeto give a residue, which

Vorschrift

To the above ketone compound, 2-(1-methylethyl)-5,9,13-trimethyl-2,4,8,12-cyclotetradecatetraen-1-one (137 mg, 0.48 mmol) in dry toluene (2.5 ml) was dropwise added with stirring on a cooling bath at -70° C. a solution of 1M diisobutyl aluminium hydride in toluene (0.6 ml). One hour later, disappearance of the starting material was confirmed. After addition of water (0.25 ml) and removal of the cooling bath, the reaction mixture was stirred, followed by drying over MgSO4, filtration, and concentration to give a residue, which was subjected to silica gel column chromatography (solvent:-hexane/ethyl acetate=12:1) to obtain the aimed sarcophytol A (125 mg, 88%).

Quelle